CN103347887A - 双核金属络合物及含有其的有机电致发光元件 - Google Patents
双核金属络合物及含有其的有机电致发光元件 Download PDFInfo
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- CN103347887A CN103347887A CN2011800666430A CN201180066643A CN103347887A CN 103347887 A CN103347887 A CN 103347887A CN 2011800666430 A CN2011800666430 A CN 2011800666430A CN 201180066643 A CN201180066643 A CN 201180066643A CN 103347887 A CN103347887 A CN 103347887A
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- 150000004696 coordination complex Chemical class 0.000 title abstract description 5
- 238000005401 electroluminescence Methods 0.000 title abstract 2
- 239000003446 ligand Substances 0.000 claims abstract description 74
- -1 atoms metals Chemical class 0.000 claims description 222
- 229910052741 iridium Inorganic materials 0.000 claims description 148
- 229910052799 carbon Inorganic materials 0.000 claims description 124
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 106
- 150000001875 compounds Chemical class 0.000 claims description 94
- 125000004432 carbon atom Chemical group C* 0.000 claims description 90
- 238000000034 method Methods 0.000 claims description 67
- 238000004519 manufacturing process Methods 0.000 claims description 59
- 125000005843 halogen group Chemical group 0.000 claims description 58
- 125000000217 alkyl group Chemical group 0.000 claims description 46
- 229910052757 nitrogen Inorganic materials 0.000 claims description 41
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 40
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 32
- VQGHOUODWALEFC-UHFFFAOYSA-N alpha-Phenylpyridine Natural products C1=CC=CC=C1C1=CC=CC=N1 VQGHOUODWALEFC-UHFFFAOYSA-N 0.000 claims description 26
- 229910052751 metal Inorganic materials 0.000 claims description 25
- 239000002184 metal Substances 0.000 claims description 25
- 125000004429 atom Chemical group 0.000 claims description 19
- 150000008048 phenylpyrazoles Chemical class 0.000 claims description 12
- 125000003118 aryl group Chemical group 0.000 claims description 11
- JVZRCNQLWOELDU-UHFFFAOYSA-N gamma-Phenylpyridine Natural products C1=CC=CC=C1C1=CC=NC=C1 JVZRCNQLWOELDU-UHFFFAOYSA-N 0.000 claims description 11
- 229910052763 palladium Inorganic materials 0.000 claims description 8
- 239000002243 precursor Substances 0.000 claims description 8
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 5
- 229910052703 rhodium Inorganic materials 0.000 claims description 5
- 229910052707 ruthenium Inorganic materials 0.000 claims description 5
- 229910052762 osmium Inorganic materials 0.000 claims description 4
- OMJKVIFSWSQTGQ-UHFFFAOYSA-N 6,7-bis(aziridin-1-yl)quinazoline-5,8-dione Chemical compound C1CN1C=1C(=O)C2=NC=NC=C2C(=O)C=1N1CC1 OMJKVIFSWSQTGQ-UHFFFAOYSA-N 0.000 claims description 3
- PCPQWYHRMVULIX-UHFFFAOYSA-P [1-[2,3-dihydroxy-4-[4-(oxoazaniumylmethylidene)pyridin-1-yl]butyl]pyridin-4-ylidene]methyl-oxoazanium;dinitrate Chemical compound [O-][N+]([O-])=O.[O-][N+]([O-])=O.C1=CC(=C[NH+]=O)C=CN1CC(O)C(O)CN1C=CC(=C[NH+]=O)C=C1 PCPQWYHRMVULIX-UHFFFAOYSA-P 0.000 claims description 3
- BTIIGNUPPKUQAP-UHFFFAOYSA-N [1-[2,3-dihydroxy-4-[4-(oxoazaniumylmethylidene)pyridin-1-yl]butyl]pyridin-4-ylidene]methyl-oxoazanium;diperchlorate Chemical compound [O-]Cl(=O)(=O)=O.[O-]Cl(=O)(=O)=O.C1=CC(=C[NH+]=O)C=CN1CC(O)C(O)CN1C=CC(=C[NH+]=O)C=C1 BTIIGNUPPKUQAP-UHFFFAOYSA-N 0.000 claims description 3
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 3
- 239000000463 material Substances 0.000 abstract description 55
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 228
- 239000010410 layer Substances 0.000 description 163
- GKOZUEZYRPOHIO-UHFFFAOYSA-N iridium atom Chemical compound [Ir] GKOZUEZYRPOHIO-UHFFFAOYSA-N 0.000 description 139
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 114
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 110
- 239000000203 mixture Substances 0.000 description 100
- 238000006243 chemical reaction Methods 0.000 description 93
- 239000002585 base Substances 0.000 description 88
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 84
- MILUBEOXRNEUHS-UHFFFAOYSA-N iridium(3+) Chemical compound [Ir+3] MILUBEOXRNEUHS-UHFFFAOYSA-N 0.000 description 78
- 239000000047 product Substances 0.000 description 74
- 239000007787 solid Substances 0.000 description 50
- 229910052786 argon Inorganic materials 0.000 description 42
- 238000005160 1H NMR spectroscopy Methods 0.000 description 41
- 238000013019 agitation Methods 0.000 description 39
- 150000003222 pyridines Chemical class 0.000 description 37
- 239000007789 gas Substances 0.000 description 36
- 239000000243 solution Substances 0.000 description 35
- 239000001257 hydrogen Substances 0.000 description 34
- 229910052739 hydrogen Inorganic materials 0.000 description 34
- 239000002904 solvent Substances 0.000 description 34
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 33
- 125000001424 substituent group Chemical group 0.000 description 33
- 239000000460 chlorine Substances 0.000 description 32
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 32
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- 125000004434 sulfur atom Chemical group 0.000 description 32
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 31
- 230000027756 respiratory electron transport chain Effects 0.000 description 31
- PQXKHYXIUOZZFA-UHFFFAOYSA-M lithium fluoride Chemical compound [Li+].[F-] PQXKHYXIUOZZFA-UHFFFAOYSA-M 0.000 description 30
- 239000000706 filtrate Substances 0.000 description 29
- 238000000434 field desorption mass spectrometry Methods 0.000 description 28
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- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 24
- 238000002360 preparation method Methods 0.000 description 23
- 229910052731 fluorine Inorganic materials 0.000 description 22
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 21
- 150000002397 1-phenylpyrazoles Chemical class 0.000 description 20
- 150000002431 hydrogen Chemical class 0.000 description 20
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical group CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 18
- 238000000926 separation method Methods 0.000 description 17
- 229910052782 aluminium Inorganic materials 0.000 description 16
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 16
- 239000000758 substrate Substances 0.000 description 16
- WITMXBRCQWOZPX-UHFFFAOYSA-N 1-phenylpyrazole Chemical compound C1=CC=NN1C1=CC=CC=C1 WITMXBRCQWOZPX-UHFFFAOYSA-N 0.000 description 15
- 239000004411 aluminium Substances 0.000 description 15
- SYSQUGFVNFXIIT-UHFFFAOYSA-N n-[4-(1,3-benzoxazol-2-yl)phenyl]-4-nitrobenzenesulfonamide Chemical class C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)NC1=CC=C(C=2OC3=CC=CC=C3N=2)C=C1 SYSQUGFVNFXIIT-UHFFFAOYSA-N 0.000 description 15
- 150000003217 pyrazoles Chemical class 0.000 description 15
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 15
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 15
- 238000001914 filtration Methods 0.000 description 14
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 13
- 239000001301 oxygen Substances 0.000 description 13
- 229910052760 oxygen Inorganic materials 0.000 description 13
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 13
- 238000010898 silica gel chromatography Methods 0.000 description 13
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 12
- 239000002253 acid Substances 0.000 description 12
- 238000004992 fast atom bombardment mass spectroscopy Methods 0.000 description 12
- 125000001153 fluoro group Chemical group F* 0.000 description 12
- 239000011521 glass Substances 0.000 description 12
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- 238000001228 spectrum Methods 0.000 description 12
- 125000001544 thienyl group Chemical group 0.000 description 12
- OQJQPIWVCBJVAZ-UHFFFAOYSA-N 1-methyl-2-phenylimidazole Chemical compound CN1C=CN=C1C1=CC=CC=C1 OQJQPIWVCBJVAZ-UHFFFAOYSA-N 0.000 description 11
- 125000005647 linker group Chemical group 0.000 description 11
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 10
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 10
- 239000008367 deionised water Substances 0.000 description 10
- 229910021641 deionized water Inorganic materials 0.000 description 10
- 238000001035 drying Methods 0.000 description 10
- 239000011737 fluorine Substances 0.000 description 10
- HZVOZRGWRWCICA-UHFFFAOYSA-N methanediyl Chemical compound [CH2] HZVOZRGWRWCICA-UHFFFAOYSA-N 0.000 description 10
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 description 9
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
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- DWUXEBVMTJBKRQ-UHFFFAOYSA-N iridium(3+) pyrazol-2-ide Chemical compound N=1N(C=CC=1)[Ir+2] DWUXEBVMTJBKRQ-UHFFFAOYSA-N 0.000 description 9
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- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 7
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- 125000004093 cyano group Chemical group *C#N 0.000 description 7
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 7
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- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 6
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- DMKQGDNBFLQYSV-UHFFFAOYSA-N [O].C(CCC)OC(CCCCCC)(OCCCCCC)OCCCCC Chemical compound [O].C(CCC)OC(CCCCCC)(OCCCCCC)OCCCCC DMKQGDNBFLQYSV-UHFFFAOYSA-N 0.000 description 6
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- CFBGXYDUODCMNS-UHFFFAOYSA-N cyclobutene Chemical compound C1CC=C1 CFBGXYDUODCMNS-UHFFFAOYSA-N 0.000 description 6
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- 125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 description 6
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- 125000000467 secondary amino group Chemical group [H]N([*:1])[*:2] 0.000 description 6
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- CUGZEDSDRBMZMY-UHFFFAOYSA-N trihydrate;hydrochloride Chemical compound O.O.O.Cl CUGZEDSDRBMZMY-UHFFFAOYSA-N 0.000 description 6
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 6
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- 125000004390 alkyl sulfonyl group Chemical group 0.000 description 5
- 239000007864 aqueous solution Substances 0.000 description 5
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 5
- 229920006395 saturated elastomer Polymers 0.000 description 5
- 125000004646 sulfenyl group Chemical group S(*)* 0.000 description 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical group CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
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- PJXISJQVUVHSOJ-UHFFFAOYSA-N indium(iii) oxide Chemical compound [O-2].[O-2].[O-2].[In+3].[In+3] PJXISJQVUVHSOJ-UHFFFAOYSA-N 0.000 description 4
- 239000000543 intermediate Substances 0.000 description 4
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- MCJGNVYPOGVAJF-UHFFFAOYSA-N quinolin-8-ol Chemical compound C1=CN=C2C(O)=CC=CC2=C1 MCJGNVYPOGVAJF-UHFFFAOYSA-N 0.000 description 4
- 239000002994 raw material Substances 0.000 description 4
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- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 4
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- XOLBLPGZBRYERU-UHFFFAOYSA-N tin dioxide Chemical compound O=[Sn]=O XOLBLPGZBRYERU-UHFFFAOYSA-N 0.000 description 4
- LEONUFNNVUYDNQ-UHFFFAOYSA-N vanadium atom Chemical compound [V] LEONUFNNVUYDNQ-UHFFFAOYSA-N 0.000 description 4
- NAWXUBYGYWOOIX-SFHVURJKSA-N (2s)-2-[[4-[2-(2,4-diaminoquinazolin-6-yl)ethyl]benzoyl]amino]-4-methylidenepentanedioic acid Chemical compound C1=CC2=NC(N)=NC(N)=C2C=C1CCC1=CC=C(C(=O)N[C@@H](CC(=C)C(O)=O)C(O)=O)C=C1 NAWXUBYGYWOOIX-SFHVURJKSA-N 0.000 description 3
- SNTWKPAKVQFCCF-UHFFFAOYSA-N 2,3-dihydro-1h-triazole Chemical compound N1NC=CN1 SNTWKPAKVQFCCF-UHFFFAOYSA-N 0.000 description 3
- NBYLBWHHTUWMER-UHFFFAOYSA-N 2-Methylquinolin-8-ol Chemical compound C1=CC=C(O)C2=NC(C)=CC=C21 NBYLBWHHTUWMER-UHFFFAOYSA-N 0.000 description 3
- GYHNNYVSQQEPJS-UHFFFAOYSA-N Gallium Chemical compound [Ga] GYHNNYVSQQEPJS-UHFFFAOYSA-N 0.000 description 3
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 3
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 3
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 3
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 3
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- 230000004888 barrier function Effects 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
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- 229910052749 magnesium Inorganic materials 0.000 description 3
- 239000011777 magnesium Substances 0.000 description 3
- 125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 description 3
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 3
- 239000002861 polymer material Substances 0.000 description 3
- IUBQJLUDMLPAGT-UHFFFAOYSA-N potassium bis(trimethylsilyl)amide Chemical compound C[Si](C)(C)N([K])[Si](C)(C)C IUBQJLUDMLPAGT-UHFFFAOYSA-N 0.000 description 3
- 238000007740 vapor deposition Methods 0.000 description 3
- UEMGWPRHOOEKTA-UHFFFAOYSA-N 1,3-difluorobenzene Chemical compound FC1=CC=CC(F)=C1 UEMGWPRHOOEKTA-UHFFFAOYSA-N 0.000 description 2
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- APSBXTVYXVQYAB-UHFFFAOYSA-M sodium docusate Chemical group [Na+].CCCCC(CC)COC(=O)CC(S([O-])(=O)=O)C(=O)OCC(CC)CCCC APSBXTVYXVQYAB-UHFFFAOYSA-M 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
- 229910000104 sodium hydride Inorganic materials 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 238000004528 spin coating Methods 0.000 description 1
- PJANXHGTPQOBST-UHFFFAOYSA-N stilbene Chemical class C=1C=CC=CC=1C=CC1=CC=CC=C1 PJANXHGTPQOBST-UHFFFAOYSA-N 0.000 description 1
- 150000004867 thiadiazoles Chemical class 0.000 description 1
- 150000007979 thiazole derivatives Chemical class 0.000 description 1
- 239000011135 tin Substances 0.000 description 1
- 229910052718 tin Inorganic materials 0.000 description 1
- 239000010936 titanium Substances 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
- 238000002834 transmittance Methods 0.000 description 1
- 150000003852 triazoles Chemical class 0.000 description 1
- WFKWXMTUELFFGS-UHFFFAOYSA-N tungsten Chemical compound [W] WFKWXMTUELFFGS-UHFFFAOYSA-N 0.000 description 1
- 229910052721 tungsten Inorganic materials 0.000 description 1
- 239000010937 tungsten Substances 0.000 description 1
- 229910052720 vanadium Inorganic materials 0.000 description 1
- GPPXJZIENCGNKB-UHFFFAOYSA-N vanadium Chemical compound [V]#[V] GPPXJZIENCGNKB-UHFFFAOYSA-N 0.000 description 1
- 238000009736 wetting Methods 0.000 description 1
- 229910052727 yttrium Inorganic materials 0.000 description 1
- VWQVUPCCIRVNHF-UHFFFAOYSA-N yttrium atom Chemical compound [Y] VWQVUPCCIRVNHF-UHFFFAOYSA-N 0.000 description 1
Images
Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F15/00—Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic Table
- C07F15/0006—Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic Table compounds of the platinum group
- C07F15/0033—Iridium compounds
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- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
- C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
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- H—ELECTRICITY
- H05—ELECTRIC TECHNIQUES NOT OTHERWISE PROVIDED FOR
- H05B—ELECTRIC HEATING; ELECTRIC LIGHT SOURCES NOT OTHERWISE PROVIDED FOR; CIRCUIT ARRANGEMENTS FOR ELECTRIC LIGHT SOURCES, IN GENERAL
- H05B33/00—Electroluminescent light sources
- H05B33/12—Light sources with substantially two-dimensional radiating surfaces
- H05B33/14—Light sources with substantially two-dimensional radiating surfaces characterised by the chemical or physical composition or the arrangement of the electroluminescent material, or by the simultaneous addition of the electroluminescent material in or onto the light source
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- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K59/00—Integrated devices, or assemblies of multiple devices, comprising at least one organic light-emitting element covered by group H10K50/00
- H10K59/30—Devices specially adapted for multicolour light emission
- H10K59/32—Stacked devices having two or more layers, each emitting at different wavelengths
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- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/30—Coordination compounds
- H10K85/341—Transition metal complexes, e.g. Ru(II)polypyridine complexes
- H10K85/342—Transition metal complexes, e.g. Ru(II)polypyridine complexes comprising iridium
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- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/30—Coordination compounds
- H10K85/361—Polynuclear complexes, i.e. complexes comprising two or more metal centers
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- C—CHEMISTRY; METALLURGY
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- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1018—Heterocyclic compounds
- C09K2211/1025—Heterocyclic compounds characterised by ligands
- C09K2211/1029—Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom
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- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1018—Heterocyclic compounds
- C09K2211/1025—Heterocyclic compounds characterised by ligands
- C09K2211/1044—Heterocyclic compounds characterised by ligands containing two nitrogen atoms as heteroatoms
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/18—Metal complexes
- C09K2211/185—Metal complexes of the platinum group, i.e. Os, Ir, Pt, Ru, Rh or Pd
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Inorganic Chemistry (AREA)
- Physics & Mathematics (AREA)
- High Energy & Nuclear Physics (AREA)
- Crystallography & Structural Chemistry (AREA)
- Electroluminescent Light Sources (AREA)
- Plural Heterocyclic Compounds (AREA)
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JP2010269627 | 2010-12-02 | ||
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JP2011-029564 | 2011-02-15 | ||
PCT/JP2011/077979 WO2012074111A1 (ja) | 2010-12-02 | 2011-12-02 | 二核金属錯体、及びそれを用いた有機エレクトロルミネッセンス素子 |
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CN2011800666430A Pending CN103347887A (zh) | 2010-12-02 | 2011-12-02 | 双核金属络合物及含有其的有机电致发光元件 |
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US (1) | US9029541B2 (ja) |
EP (1) | EP2647642A1 (ja) |
JP (1) | JP5900346B2 (ja) |
KR (1) | KR20130122763A (ja) |
CN (1) | CN103347887A (ja) |
TW (1) | TW201251002A (ja) |
WO (1) | WO2012074111A1 (ja) |
Cited By (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
TWI667326B (zh) * | 2014-05-29 | 2019-08-01 | 德商西門斯股份有限公司 | 雙核磷光發光體、有機電層、有機半導體組件、製造有機電層之方法、及有機電層之用途 |
CN111269270A (zh) * | 2020-02-28 | 2020-06-12 | 江苏大学 | 一种中性双金属配合物铱-双苯并咪唑晶体材料及其制备方法和应用 |
CN114853816A (zh) * | 2022-04-28 | 2022-08-05 | 京东方科技集团股份有限公司 | 金属配合物、包含其的有机电致发光器件及显示装置 |
Families Citing this family (7)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2014175616A (ja) * | 2013-03-12 | 2014-09-22 | Ube Ind Ltd | 二核イリジウム錯体を発光層に含む有機エレクトロルミネッセンス素子 |
JP6468579B2 (ja) * | 2013-05-10 | 2019-02-13 | 国立大学法人山形大学 | 青色有機エレクトロルミネッセンス素子 |
JP6131712B2 (ja) * | 2013-05-21 | 2017-05-24 | 宇部興産株式会社 | 二核金属錯体化合物、及びこれを使用した有機エレクトロルミネッセンス素子 |
CN103360429B (zh) * | 2013-07-23 | 2015-09-30 | 南京理工大学 | 环金属铱光敏剂、合成及其在光催化还原水出氢的应用 |
KR102290674B1 (ko) | 2013-08-26 | 2021-08-19 | 가부시키가이샤 한도오따이 에네루기 켄큐쇼 | 발광 소자, 발광 장치, 표시 장치, 조명 장치, 및 전자 기기 |
JP2015193572A (ja) * | 2014-03-31 | 2015-11-05 | 宇部興産株式会社 | パーフルオロアルキル基を含むビベンズイミダゾール化合物、およびその製造方法 |
WO2018165134A1 (en) * | 2017-03-06 | 2018-09-13 | Thje Board Of Regents Of Oklahoma State University | Method for the synthesis and isolation of facial-tris-homoleptic phenylpyridinato iridium (iii) photocatalysts |
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US20030152802A1 (en) * | 2001-06-19 | 2003-08-14 | Akira Tsuboyama | Metal coordination compound and organic liminescence device |
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-
2011
- 2011-12-02 TW TW100144424A patent/TW201251002A/zh unknown
- 2011-12-02 CN CN2011800666430A patent/CN103347887A/zh active Pending
- 2011-12-02 JP JP2012546961A patent/JP5900346B2/ja not_active Expired - Fee Related
- 2011-12-02 EP EP11845105.3A patent/EP2647642A1/en not_active Withdrawn
- 2011-12-02 US US13/990,928 patent/US9029541B2/en not_active Expired - Fee Related
- 2011-12-02 KR KR1020137016884A patent/KR20130122763A/ko not_active Application Discontinuation
- 2011-12-02 WO PCT/JP2011/077979 patent/WO2012074111A1/ja active Application Filing
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US20030152802A1 (en) * | 2001-06-19 | 2003-08-14 | Akira Tsuboyama | Metal coordination compound and organic liminescence device |
CN101065359A (zh) * | 2004-10-01 | 2007-10-31 | 宇部兴产株式会社 | 双核金属络合物、金属络合物色素、光电转换元件及光化学电池 |
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WO2009154275A1 (ja) * | 2008-06-19 | 2009-12-23 | 宇部興産株式会社 | 二核ルテニウム錯体色素、ルテニウム-オスミウム錯体色素、当該錯体色素を有する光電変換素子、及び光化学電池 |
WO2010055856A1 (ja) * | 2008-11-12 | 2010-05-20 | 宇部興産株式会社 | 二核金属錯体色素により増感された半導体微粒子と、イオン液体を主成分とする電解質溶液とを備える光化学電池 |
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TWI667326B (zh) * | 2014-05-29 | 2019-08-01 | 德商西門斯股份有限公司 | 雙核磷光發光體、有機電層、有機半導體組件、製造有機電層之方法、及有機電層之用途 |
CN111269270A (zh) * | 2020-02-28 | 2020-06-12 | 江苏大学 | 一种中性双金属配合物铱-双苯并咪唑晶体材料及其制备方法和应用 |
CN111269270B (zh) * | 2020-02-28 | 2022-06-21 | 江苏大学 | 一种中性双金属配合物铱-双苯并咪唑晶体材料及其制备方法和应用 |
CN114853816A (zh) * | 2022-04-28 | 2022-08-05 | 京东方科技集团股份有限公司 | 金属配合物、包含其的有机电致发光器件及显示装置 |
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Publication number | Publication date |
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EP2647642A1 (en) | 2013-10-09 |
JPWO2012074111A1 (ja) | 2014-05-19 |
US20130324733A1 (en) | 2013-12-05 |
US9029541B2 (en) | 2015-05-12 |
JP5900346B2 (ja) | 2016-04-06 |
KR20130122763A (ko) | 2013-11-08 |
WO2012074111A1 (ja) | 2012-06-07 |
TW201251002A (en) | 2012-12-16 |
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